


50 Year Old Virgins

by AgentGmy



Category: Endgame - Fandom, Marvel, Marvel Cinematic Universe, The Avengers (Marvel Movies), The Avengers (Marvel) - All Media Types
Genre: Avengers: Endgame (Movie), Endgame
Language: English
Status: Completed
Published: 2019-04-24
Updated: 2019-06-08
Packaged: 2020-01-25 20:51:09
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 2,858
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18582364
Author URL: https://archiveofourown.org/users/AgentGmy/pseuds/AgentGmy
Summary: Lifelong friends Jeremy and Paul have a bet: who will be the last to lose their virginity? This bet has been 35 years in the making, although it may soon end with Paul's upcoming marriage. Jeremy, who has never had much luck in dating, come up with a plan to keep his virginity intact, but maybe at the expense of Paul's happiness.





	1. Walking Home

**Author's Note:**

> This is based off of the shenanigans of Jeremy Renner and Paul Rudd during the Avengers:Endgame press tour. It is how I imagine a comedy movie with Renner and Rudd as the lead roles to pan out. While I use the names Jeremy and Paul in the text, it simply means that the actors would be playing those characters, not that the actors are represented by the characters. Please let me know if you have any suggestions!

The smooth rhythm of Thelonius Monk seeped from the windows of Blindshot, the local bar for individuals who preferred a stench other than vomit. This was a place that Jeremy frequented often, not because he was an alcoholic, (well maybe he was, but that conversation is for a different time), but because he was a part-time bartender. Two nights and four days a week were dedicated to serving the patrons of downtown Milwaukee. 

Since today was a Tuesday, Jeremy had an afternoon shift. Most of the customers were either lost tourists or older couples, all of whom exited the vicinity sober. Well, there were always a few of the regular alcoholics, but at least they were predictable and remembered his name. As the clock ticked closer to 6:00 pm, Jeremy started wiping down the bar to prepare for the next bartender's shift. He then began to wash the precarious stack of glasses that had piled up throughout the previous few hours. At 6:09, the other bartender finally arrived. Grateful, Jeremy slung his messenger bag, which had been slouched behind the counter, over his shoulder and headed out the door. The soft jingle trailed behind him as he began to walk back to his one-bedroom apartment. 

I should get something to eat, Jeremy thought to himself as he whiffed the fragrance coming from the family-owned pizza parlor down the street. But the reminders of his best friend's wedding nagged at the back of his head. Even though he wasn't the groom, he still wanted to look his best. It had been six months since the two had last seen each other, and Jeremy wanted to make their first reunion a surprising one. Since middle school, Jeremy had been the "chunky" one. Sure he played football, but he had always envied his friend's leaner swimmer's body. Post-college, his woes only got worse. The number on the scale became a roller coaster that mirrored his levels of stress. Luckily, things were finally looking up after acquiring the bartender job. Not only was it a lot more active than his previous sedentary office job, but it also allowed him to dedicate more time to regular exercise. Currently, he was an avid fan of handball. He had reluctantly joined the rec center's intramural team after a ex-girlfriend had gifted him a coupon, but he soon realized that the sport was so much more than he had expected. With its fast paced passing and running, the extra pounds that had been storing up over the winter soon melted away.

Jeremy's friend was flying back from New York next week. As a business executive, he had spent several months negotiating a deal in the Big Apple, but he would be returning back to his hometown for the wedding. Jeremy was largely in charge for making sure that things ran smoothly at the Milwaukee end, and so far the outdoor pavilion had already been confirmed. The DJ, catering, and photography had also been arranged.

These plans swirled around in Jeremy's head as he continued his hungry journey home. The meal-prepped chicken and asparagus waiting in the fridge suddenly didn't seem as appetizing. One more month, he reminded himself. After the wedding maybe, just maybe, he could be a little more lax. 

As he was trudging up the front steps, Jeremy stopped dead in his tracts. One of the flyers had reminded him of an urgent matter: the bachelor party. Did I even plan the bachelor party? He thought he would have remembered booking anything that extreme. After some careful pondering, he concluded that he had definitely not planned the bachelor party. Thankfully, he still had one more week.

As a master at dealing with things later, that was exactly what Jeremy planned to do about the party. His feet ached from standing up all day, and the last thing he wanted to do was planning. Instead, he microwaved his limp chicken and limper vegetables, then sat himself down in front of his not-fully-installed TV. The screen itself was a respectable size, but the fact that it still sat on a half-built Ikea media center spoke volumes about his time management. Jeremy struggled to found the remote among the newspaper-ridden couch, but when he did find it, he immediately found a nature documentary that piqued his interest. At the very least, the idea of the documentary was intriguing. Alas, he fell asleep before he could learn about the wondrous penguins of South America. The TV's lights continued that flash brightly throughout the night, even after the show had transitioned into a flashy superhero movie.


	2. Night In

With his feet propped up on the coffee table, which was an island of bridal magazines amidst an otherwise orderly living room, Paul scrolled through various channels. Skipping over old cartoon reruns and a hardly watched eight-o'clock news network, he finally settled on a good ole superhero movie. Never too old to enjoy one of these, he thought to himself. Just as the climax was beginning to build (the villain had just revealed themselves to the group of ragtag heroes), the front door creaked open.

"How was it?" Paul asked as he looked up to see his fiance's glowing face. As, she took her heels off, he admired her navy jeans and white crochet top. Although it seemed like something Forever 21 model would sport, he thought she pulled it off.

"Well you know I can't tell you," Valerie responded, putting on a pantomimed poker face. However, it did not stop her smile from peering through. "Fine," she squealed, giving in, "it fit perfectly!"

"Any dress would," Paul smoothly responded. Valerie set her bag on the kitchen table, crawling onto the couch to lay her head on Paul's chest.

"September 20th can't come soon enough," she said. Their eyes both glanced towards the bolded date on the lopsided calendar that hung to the right of the television. The four x's at the beginning of the calendar revealed that today was September 5th.

"I think all of our plans are set," Valerie whispered, "except for one." The movie's explosion sounds were suddenly overtaken by the sound of the two kissing, and he immediately knew what she was referencing. The wedding night for any couple is a momentous occasion, but as relatively devout Christians, Paul and Valerie had both sworn off premarital sex. Eleven years of strictly lip-locking meant that they were both anticipating the big day, or more realistically, the big night.

"You ready?" Valerie bit her lip, staring into her soon-to-be life partner's eyes.

"For the wedding?"

"No, after," she smirked, raising an eyebrow.

"Of course!" Although his tone was firm, his gaze faltered slightly. Valerie picked up on it, but she chalked it up to nerves. First times were always came with its anxiety, and it didn't help that their combined ages were almost tipping 90.

Valerie ran her hands through his remarkably black hair. "You'll be fine. I mean, what's the worst that can happen?"

"You're right, I'm just overthinking things. You know how it is with me." Paul intertwined his hand with Valerie's other hand, rubbing his thumb against hers.

Valerie tucked her knees against Paul's body, still laying her head against his chest and closed her eyes. As he stared at her resting body, he realized that this was truly the woman he loved. They both went to the same college, but they had never been single at the same time. It wasn't until an economic conference when their paths crossed again. After many meetups to discuss potential business collaborations, their relationship finally turned into something more. And although they had their fair share of breaks, eleven years was well worth the wait, Paul thought. 

After he was sure she was asleep, his gaze returned back to the movie. The characters fought battle after battle, but ultimately, the heroes ended up losing.


	3. Welcome Home

Stepping out of the gate, the airport’s massive walkways were relatively empty. Only the determined or desperate wanted to be arriving at 4:30 am. Red-eye flights weren’t exactly Paul's idea of a good time, and while he could afford to book a ticket for a better time, childhood experience had numbed him from the tiredness. Besides, the sooner he got to Milwaukee, the more time he had to prepare for the wedding and spend time with Jeremy. He missed his childhood best friend’s snarky humor, something he didn’t get enough of in New York.

Paul rounded the corner to the normally crowded area where drivers and visitors stand to pick up the passengers. Today, there were only a couple of people holding up signs.

“Glad that New York hasn’t made you any taller,” said a familiar voice from beneath a hoodie.

“Jere, how’s it been?” Paul found the other man holding the sign with his name on it upside down.

“Same old same old. And you?”

“I’m tired, but excited. I know that you have something incredible planned!”

“Sure thing… It’ll be you, me, and the others against the world, just like the good old days.”

And that's the way Paul preferred it. A small group of consistent friends was what every introvert like Paul needed. They had been together ever since that fateful day in ninth grade English, when they were all forced to reenact a scene from Romeo and Juliet. Because there were more boys than girls in the class, Jeremy was forced to don a wig and be Juliet. If cell phones had been commonplace back then, there’s no doubt that the video would’ve been posted onto YouTube. In addition to Paul, the other members of the group were Sean, Morgan, and Allen, who were also Paul's groomsmen. 

“Why don’t you to love birds just get married already?” Valerie laughed as Jeremy and Paul hugged.

“If we were gay, I would’ve fucked him years ago,” Jeremy snickered.

“Oh, don’t be so sure that he isn’t,” she countered. “Have you seen the way he stares at your ass?”

“Damn right,” Paul smirked.

With that, the trio made their way to the underground parking lot, then to Jeremy’s beat up sedan. The ride to Jeremy’s apartment was far from silent, as the couple recounted their favorite moments from New York. In turn, Jeremy updated them on all the interesting gossip that had occurred during their three month absence.

“Taryn did what?” fiance’s mouth dropped.

“Okay, so maybe she didn’t exactly sleep with the CEO, but that’s what she was getting at.”

“I bet she was drunk off of her ass though,” Paul laughed.

“Oh, definitely. Doesn’t change what she said though. She definitely has a thing going on with him.”

At 5:17 am, the car parked itself in front of the apartment complex. Valerie took all of the luggage up on the elevator, but Paul elected to join Jeremy with taking the stairs, as it was apparently “good cardio”.

“Are you ready to lose?” Jeremy asked as they were in between floors two and three.

“What do you mean?” Paul feigned obliviousness.

Jeremy whistled, making an obscene hand gesture. “The pact.”

What Jeremy was referring to was the infamous pact, one that has had been in place since sophomore year of high school. It had started out between Paul, Jeremy, Sean, Morgan, and Allen, but currently, only Jeremy and Paul were in the running. Their fifteen-year-old selves decided that they were too mature for sex (more realistically, they needed an excuse for why they weren't getting any), and thus created an anti-sex pact. Whoever was last to lose their v card got, well...something. Pride was enough to tide the adolescents over, but as the years went by, a monetary incentive was added. Sean, Morgan, and Allen had all started families of their owns, relinquishing their chance at the now $15,000 prize. However, Paul never really found a soulmate (until now), and Jeremy was too stubborn to give in.

“Ah, that. I mean unless something happens within this week, there’s nothing I can do.” Paul responded.

“And she doesn’t know?”

“Of course she doesn’t know! She thinks I’m some Jesus-loving catholic boy or something. Do you know what it’s like trying to out-church her on Sundays?”

“Are you going to tell her?”

“We’ll see.”

At this point, both men were breathing pretty hard, and they resigned to silence. Eight flights of stairs was not kind to their middle-aged bodies. Valerie was leaning against the apartment door when Paul and Jeremy finally crested the last of the stairs.

“You know where the key is,” Jeremy managed to get out between huffs of breath.

“You’re the host,” she responded, moving out of the way so that Jeremy could unlock the door.

“Sorry about the mess by the way, I tried to tidy up a little bit, but…”

The door swung open to reveal a surprisingly clean living room. But little did the guests know about the horrors wedged behind the closet doors. Paul and Valerie made their way to the guest bedroom (which was usually Jeremy’s hobby space), as Jeremy went to the kitchen to make pancakes.

“Chocolate or blueberry?” Jeremy asked out of consideration, already grabbing the bag of chocolate chips.

“Chocolate,” their unison response echoed from the bedroom.

The two emerged just as Jeremy was flipping the last of the pancakes. Paul helped himself to the plate stacked the highest, then opening a cabinet to get the fake maple syrup out.

“Thanks for this by the way. I know we still have a place here, but given that it’s only semi-furnished, this is a huge help. Less stress, you know?” Valerie said, grabbing forks from a drawer.

“Of course. As best man, it's my job, isn’t it?” Jeremy stole the maple syrup from Paul’s hand.

“Hey!” Paul protested.

“Carbs are bad. I’m just trying to help you out,” Jeremy chuckled, sliding the bottle back to Paul. Jeremy raised a forkful of pancakes. “Welcome home.”


	4. Game Plan

The next few days were a flurry of excitement and preparation. Jeremy and Paul, along with the rest of their friend group, went to the tailor to pick up their suits. The group of five comfortably fit into Sean’s minivan, which meant that Sean was the driver. He was also, and had always been, the one in the group who had his shit together. In high school, they had relied on for homework help, to which he always obliged. He graduated top 10% at the University of Wisconsin, then returned back to Milwaukee to utilize his civil engineering degree. Sitting in the shotgun seat was Paul. Directly behind Paul was Morgan, who was restlessly shaking his foot. Morgan was a high school chemistry teacher, as well as the team’s basketball coach. Finally, sandwiched between Jeremy and Morgan, sat the ever-quiet Allen, who had recently celebrated a promotion as the new chief of staff at the history museum.

The wedding’s colors were lavender and silver, but the group collectively decided that a lavender suit was not the way to go. Instead, they would be wearing lavender dress shirts with grey suspenders and ties. As a stickler for tradition, Paul decided to wear the standard black suit, although a purple-with-silver-accents pocket square would keep with the theme.

Sure enough, when the five men walked into the tailor, they were given five garment bags that contained the desired attire. Thankfully, there were no mishaps, although Jeremy was happy that the suit fit slightly looser than before. Bags in hand, the group headed back to the car, and then back to Jeremy’s apartment to discuss the bachelor party.

“My vote is for karaoke,” Jeremy suggested.

The four groomsmen were sitting around the coffee table, with Paul blindfolded and earmuffed in the corner.

“I can still hear you guys!” Paul yelled out into the air.

“My vote is for karaoke,” Jeremy suggested slightly quieter. Unfortunately, Jeremy had what most people referred to as a naturally loud voice.

“I’ve always wanted to try paintball,” Morgan said.

“Aren’t we a little old for that?” Sean asked, gesturing towards the group’s collective beer bellies, “and not in peak physical condition?”

“We can just do both,” Allen said. “Paintball in the afternoon, then karaoke after it gets dark.”

“Karaoke bar?” Morgan asked.

“What else?” Jeremy laughed, “although anywhere pales in comparison to Blindshot.”

A collective groan came from the three guys, while Paul was absentmindedly spinning in a spinny chair.

“Since he’s still blindfolded,” Allen perked up, whispering, “is he going to lose the pact?”

“Oh yeah, Jeremy my man!” Morgan patted Jeremy on the back.

“Let’s be real, we all thought Paul would win though,” Sean said.

“What guys? You betted against me?” Jeremy gestured in mock offence.

“You do work at a bar!” Paul shouted from across the room. The other guys looked up in shock, forgetting that Paul could technically still hear them. “Can I just take these off already, it’s getting hot.” Without waiting for their response, Paul proceeded to get up, taking off the blindfold. “Paintball sounds fun, as long as you don’t mess up this pretty face,” he said, posing.

“So we have a game plan for tomorrow?” Jeremy asked.


End file.
